


Trip to the Principals office

by fromacloset



Series: Roleplay [2]
Category: Supernatural
Genre: Aftercare, Dildos, Dom Sam, F/M, Humiliation, Light Bondage, Light Dom/sub, Oral Sex, Orgasm Denial, Porn With Plot, Roleplay, Sem-Dom Dean, Smut, Spanking, Teacher/Student Roleplay, Teasing, Vaginal Fingering, panties as gag, school girl uniform
Language: English
Status: Completed
Published: 2017-06-09
Updated: 2017-06-09
Packaged: 2018-11-11 12:23:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,164
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11148336
Author URL: https://archiveofourown.org/users/fromacloset/pseuds/fromacloset
Summary: The reader always wanted to do teacher/student roleplay and the boys help out





	1. Principal's office

You loved living with the boys. You loved that everyone is so open about things…like porn. Which was kind of an accident to be that open about. However the boys walked in on you watching porn. And boy oh boy, did that peak their interest. Well, mostly Dean at first, Sam was a little bashful at first. You told them you always wanted to roleplay. 

“What kind?” Sam asked.

“Well, I was always a good girl in school. So, I guess, like being sent to the principal’s office.”

“Huh” Dean smirked.

And that’s how you ended up in your room, putting on a school girl’s outfit. Skirt extremely shorty. You made sure the shirt was tided a little Baby one more time. Few top buttons undone. You even grabbed a black sweater. Made sure the socks were knee high and slipped your shoes on. You put your hair in a high ponytail, took one last look in the mirror and smiled.

You walked out of your room and down the hall. There was chair sitting outside a room and you smirked. The boys took care of setting up the scene and room. All you had to do was get ready. The door opened and Dean stepped out in a suit, blue tie.

“Miss Y/L/N, Principal Winchester is ready for you.” 

“Yes Mr. Winchester” you stood up and walked past him. 

Sam was sitting up right at his desk, hands folded on the table. He too was wearing a suit and a red tie. Dean closed the door and Sam gestured for you to sit in the chair. You did, with your legs closed, ankles tucked behind. Dean went and stood a little behind Sam, leaning against the wall, arms crossed.

“Miss Y/L/N” Sam spoke. “Do you understand why you have been called to my office?” 

“No, sir” you said innocently.

“Mr. Winchester told me you were distributing his class”

“Whatever do you mean?” you said to Dean, smirking a little.

“Young lady, do you find this funny?” Sam spoke. Well, that got you wet.

“Why don’t you tell Principal Winchester what you did?” Dean spoke. You looked at Sam.

“Honestly sir. I was being a good girl. I can’t imagine I did anything to disrupt the class.”

“Oh no?” Sam said raising an eyebrow. “I have a report here from Mr. Winchester, stating that you “forgot” to wear underwear to class.” You looked at Dean and blushed a little. His face was stern, but you could tell he wanted to crack. You looked back at Sam.

“Principal Winchester, they are just so constricting. It’s not healthy to have your vagina covered all the time.” You said as a matter of factly. 

“Is that so?” Sam leaned in, hands still folded. “Young lady, it is against dress code to go without any underwear or panties” without thinking you let out a little whimper. Dean raised an eyebrow. Sam cleared his throat to get your attention. “Some, including Mr. Winchester finds it very distracting.”

“Well then, Mr. Winchester should not let his eyes wander” You said.

“You leave me no choice, but to punish you.” Sam said.

“He’s lying” you shrugged.

“If I am, then please, open your legs and let Principal Winchester see for himself” Dean said standing up straight and walking towards the desk. You looked down.

“Now please” Sam said.

You placed your hands on either side of the arm rests, sat up straight and slowly opened your legs, revealing your arousal. Sam tsked and pushed his chair back.

“It seems Mr. Winchester was telling the truth.” You went to close your legs. “Keep those open” Sam ordered and you did. Sam turned his attention to Dean. “Mr. Winchester, is this how she presented herself in your class room.”

“Yes sir.” Dean said.

“What do you feel would be the appropriate punishment?” you let out another whimper and both men looked right at you.

“Are you enjoying this?” Dean asked you.

“N-no Mr. Winchester” you said. 

“Hmmmm.” Sam said getting between the chair you were in and his desk. He crouched down and looked, resting his hands on your hands. “Tsk. Tsk. Tsk. Such a naughty girl.” He said looking you directly in the eye.

“Principal Winchester, I feel a spanking would be a good start.” Dean spoke you. Sam got close to your clit and lightly blew, making you more wet and then he stood up. 

“I agree” Sam said. “Miss Y/L/N, please stand up, hands on my desk.” 

Sam moved aside and you did as you were told. Sam lightly patted your left thigh to get your legs further apart. He rubbed a hand on your back. “Naughty young ladies who tease teachers need to learn a lesson. Don’t you agree?” he whispered in your ear.

“Yes sir” you said.

You looked up when you heard a smack and saw Dean standing there hitting a ruler in his hand. You watched as he walked around and got to behind you. Bent over, your skirt rid up and your ass was perfect view. 

“You’re going to count. Ten from Mr. Winchester. Am I clear?” Sam asked you.

“Yes sir.” WACK! The first hit was hard and you yelped. “One.” You said. WACK! “Two” you counted ten. Your head looking down and you panting. 

“Are you sorry for being such a tease?” Dean asked.

“Ye-yes Mr. Winchester. So-sorry Mr. Winchester” you said.

Sam asked you to stand up and you did. He had you sit on his desk, legs spread. You winced a little when your ass hit the cold table. You leaned back on your elbows and spread your legs. You were spread so when he sat back at his chair, he had perfect view.

“That will be all for now Mr. Winchester. I will have her stay like this while I make some calls” Sam said to Dean. Dean nodded and you looked at him with pleading eyes.

“Miss Y/L/N, if you did not want to be punished then perhaps you should have worn panties in my class.” Dean said.

“Mr. Winchester, I would like you back in my office in ten minutes. Please bring those black lace panties I know this young lady has.” Sam said and Dean nodded and left. 

“Principal Winchester” you spoke.

“I need to make some calls; you will stay like this while I do so. You will not talk, can you do that?” Sam asked you.

“Yes sir.”


	2. Punishment

You sat with your legs spread, Elbows on the desk. Sam wasn’t kidding. He picked up the phone and called someone about a case they were working on. He still kept the professional manner. He looked at you when you whimpered a bit.

“I see” Sam said on the phone. He ran his finger up and down your wet slit. Your mouth opened, but no sound came out. “Yes, very good. Seems like you got it covered. Alright. Bye.” Sam hung up and turned his attention to you. Dean walked back in. “Mr. Winchester, welcome back.” 

“I got the panties.” Dean said.

“Good. If she won’t wear them for their proper use, then I guess we’ll have to find another use.” Sam said. Dean bunched them up and stroked your cheek.

“Open up” he said. Some of your arousal started to trickle down. You opened your mouth and Dean stuffed the panties in as a gag.

“That’s better” Sam said loosening his tie “It appears this young lady is very aroused by all of this. Mr. Winchester, do you feel that she should be enjoying this?" Sam” asked.

“Absolutely not.” He said. Sam picked up the ruler and lightly tapped it on your clit.

“Hn. Hn. Hn. Hn.” You whimpered.

“Miss y/L/N, if you cum without permission, you will unfortunately fail my class.” Dean said. he looked down. “Principal Winchester.” Sam stopped hitting you with the ruler. “It appears that Miss Y/L/N, also forgot to wear a bra.”

“I see. Since you have failed to dress appropriately, I suggest you read the rule book. From cover to cover. Do you feel that would be appropriate Mr. Winchester?” Sam asked.

“I do. However since Miss Y/L/N, wants to disrespect the dress code, we should give her what she wants.” You looked at Dean. “ Stand up and take off your uniform.” 

You slowly got off the desk and walked around to the front. Sam and Dean watched as you started to unbutton your shirt. You let it fall off and to the ground. You then undid the skirt and let it fall to the floor. You stepped out.

“Shoes and socks as well” Sam said sternly. 

You slipped out of your shoes and placed one foot on the chair and rolled down the sock and took it off. You did the same with the other and looked at them.

“Young lady, we want your clothes folded neatly.” 

You picked up your clothes and folded them neatly on the desk. Dean placed a suction dildo on the chair had you sit on it.

“Hmmm” you whined as he helped you lower yourself on it.

“There’s a good girl.” Dean said patting your shoulder. 

Sam grabbed a school rule book. An actual school rule book . He took of his tie and so did Dean.

“Young lady as your punishment, you will read this book. Every page, you will rise and lower yourself back on the dildo. Not every page you turn, but every page you start reading. This includes the cover and table of contents. Do I make myself clear?” you nodded.

Dean took the ties and started to tie your ankles to the chair. You whimpered and looked up at Sam. He rubbed a hand on your cheek.

“shhh. Now, Mr. Winchester and I will watch you while we work.”

“Again, no cumming without permission” Dean reminded you.

You looked at the cover page, lifted yourself and slid back on the dildo with a whimper and opened the book. Both boys praised you. They watched you read the first few chapters, whimpering and moaning. Sam would stand over your shoulder and look down at you while you read. This made you more wet. Tears started to fall, you really wanted to cum.

“Are you alright, Miss Y/L/N.” Dean asked rubbing a hand on your back, you knew that he was not only asking for the scene, but also checking in on you. If you said no, they would stop. You nodded. “Good girl.” 

When you were done, tears streaked your face, you stomach was clenched, you needed the release and both boys knew it. Dean tapped your chin and you opened your mouth. He took the panties out of your mouth and you let out a sob.

“PLEASE! MR. WINCHESTER, PRINCIPAL WINCHESTER. PLEASE! I NEED TO CUM. I’VE LEARNED MY LESSON.” 

“We believe you.” Sam said as Dean untied your ankles. 

You were shaking when Sam helped you up and laid you on the desk, legs spread and you dripping. Sam rubbed your clit and you screamed.

“Young lady, Mr. Winchester is going to let you cum, since you have passed your test. I don’t want to see you in my office again. Understand?” 

“Ye-ye-yes.” You said.

“Good girl.” 

Sam walked and started to clean up. Dean lowered his head and flicked his tongue against your clit. You gripped the table and whimpered. Just then his tongue was on you licking and his mouth was sucking.

“AAAAAAHHHHH!” you screamed. 

“I’m sorry we had to punish you, but you were such a naughty girl” Sam said.

“Please” you whimpered quietly. 

“Anything for you baby” Dean said against you. Dean thrusted two fingers in you and sucked on your clit until you came screaming. You went limp and breathed heavy. Sam was by your head, stroking your hair.

“Shhhh. Just breathe. You did so good. You were so good. Y/n, that was amazing.” He whispered in your ear. Dean grabbed a cloth and cleaned you up gently.

“Sweetheart, I’m going to lift you up now and we’re going to put some cream on your ass.” You whimpered and nodded. Dean lifted you in his arms, cradling you to his chest. “We didn’t hurt you too much, did we?” 

“No” you mumbled. 

Dean lightly laid you down on your stomach. There were some marks on your butt. Sam opened the cream and Dean rubbed a hand on your back while Sam put the cream on the marks.

“We are so proud of you” Dean whispered in your ear and you nodded and smiled.

“I should get sent to the principal’s office more.” You mumbled and both boys chuckled. 

“Only if you’re a naughty girl.” Sam said covering you with a blanket.

The boys got on either side of you and watched you as you rested and fell asleep with a goofy grin on your face.


End file.
